The ongoing global economic difficulties and the subsequent increases in unemployment have led the UK government to explore innovative ways of combating youth unemployment (i.e. young people aged 16-24 years who are not in employment, education or training (NEET)). As part of this strategy work-integration social enterprises (WISEs) have become providers of employment enhancement programmes (EEPs) that aim to improve the employability of NEETs. However, such ‘one-size-fits-all’ approaches to employability programmes overlooks the heterogeneous nature of the NEET cohort, meaning that drop-out rates are often high. This research study explores this phenomenon through a theoretical framework centred upon emotional resilience, and specifically self-regulative efficacy. The research adopts a longitudinal, mixed-methods approach that includes self-efficacy scales and semi-structured interviews to understand the impact of emotional resilience on the success of three employability programmes on NEET programme completion rates. A total of 139 NEETs participated in the research and the data demonstrates that self-regulative efficacy is a significant predictor of NEET programmes drop-out, and that their lack of emotional resilience is grounded in their chaotic family and social lives. The results have important implications for employability programmes around the world and are discussed in relation to the design of such programmes for the Caribbean.